7 Rules For Travelling With The Boss

Travelling with your boss is one of those make-it or break-it situations that can do wonders for (or, conversely, damage) your career. Knowing how to handle yourself can mean the difference when it comes time for a promotion. Nail it and you’ve got a shot. Blow it and, well, let’s just hope you’re happy with the cube by the shredder.

I learned how to travel with bosses by doing it. Fortunately, I was with coworkers, so in the early stages, I got to observe what I think are the best practices, the results of which are this week’s 7 Rules.

Rules for Travelling With The Boss

Rule #1 – Go with It

Everyone travels a little differently. Some people cram their days with 17 hours of meetings; others line up golf, dinner, drinks and all manner of extracurricular activities. Either way, the schedule is probably based on your boss’s preferences, client needs or a combination of both. No matter what activity is proposed, go with it. If you’ve never golfed, admit it, but don’t use it as an excuse not to go. Feel like sitting in your room and watching TV instead of going out for drinks with that old client? Don’t. Chances are your boss asked you to come along because he or she wants to expose you to those relationships and give the client a better idea of who you are. Suck it up and go. You can watch TV when you get home.

Rule #2 – Get Personal

Traveling usually means down time—at the airport, in the cab, waiting to check in. Use the time to get to know your boss and, perhaps more importantly, letting him or her get to know you. Office relationships can be shockingly impersonal—quick, tell me the birthday of the person sitting next to you without asking HR. Travel takes you out of that pure-business dynamic. Don’t be afraid to open up a bit or ask questions. Obviously there are lines you don’t cross—no one wants to hear about your adventures with ring worm in high school—but travel is a great excuse to learn a little bit more about the person signing your paychecks and letting them see you as more than just a cube jockey.

Rule #3 – Be Helpful

Go out of your way. Pick up the presentation from the printers. Carry the projector. Make your boss’s life a little easier. You’re still the junior guy, even on the road. If someone needs a lift, offer to call a cab. If you agree to meet in the lobby at eight, be there at 7:45. You want to be the one who makes sure the trip goes smoothly. However, that said…

Rule #4 – Don’t Be a Chump

There’s a fine line between being helpful and being a chump. It’s easy to want to do too much, so much that you end making yourself look like an intern. You’re there to show that you deserve to be. So, yes, go the extra mile, but play up a level too. Get to the meeting 15 minutes early, stay 15 minutes late, but don’t offer to take the trash out in the office. Find the line and toe it.

Rule #5 – Have One Less

One less beer or one less glass of wine at dinner. Don’t make a big deal out of it, but don’t be remembered for being the guy who got drunk at the restaurant. Don’t be remembered as the guy who made 12 trips to the buffet. Be remembered for your skills, your aptitude, your ideas and your personal professionalism. Don’t be remembered for things you don’t want to be remembered for. Don’t embarrass your boss. Go along for anything (see: Rule #1), but don’t lead the charge. Your behaviour, ultimately, reflects on your boss. Make that reflection gleaming.

Rule #6 – Skip the Friends

You may not have seen your college roommate since he moved to Melbourne, but don’t take the business trip as an opportunity to see him. It may be convenient to visit family or friends while on the road with the boss, but convenience alone does not make it right. You want to be around with your boss. You want to be there if the opportunity to spend more time with a client or investor comes up. If you have plans with friends and a late dinner with the boss comes up, you’re going to end up disappointing someone. If you absolutely need to see someone, make arrangements to stay an extra day. Keep the business trip about business.

Rule #7 – Don’t Talk About It

Maybe your boss had one too many, maybe a client did something embarrassing. Whatever it is, don’t talk about it when you get back to the office. There’s an understanding that goes along with business travel—what happens on the road stays there. This isn’t to say that anything necessarily happens, it’s just that you don’t want to put yourself in a position to be talking behind the boss’s back. Lips sealed. Keep the recaps business-related. You just might get invited back.

Have you had any disastrous trips with your boss comment below and let us know what rules would you add to the list?